Conceptualizations of safer sex practices among young gay men (YGM) are frequently structured around communication between partners and the subsequent utilization or absence of condoms in a sexual encounter. Drawing on a sample of 34 in-depth interviews with YGM, ages 18 to 24, the authors explore the ways in which conceptualizations and definitions of safer sex are discussed and enacted. Placing attention on their safer sex practices, the authors analyze the conversations that do and do not occur among YGM and their partners, including the strategies (e.g., negotiated safety, condom communication and negotiation) that are commonly perceived as most useful by YGM. The authors provide recommendations regarding how to craft safer sex messages for YGM by considering their competing demands.